Potassium Carbonate → 3-(Dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol

HRID 1166530Notes

Reaction equation

HRID 1166530 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl.[CH3:9][N:10]([CH2:12][CH:13]1[CH2:22][C:21]2[C:16](=[CH:17][C:18]([O:23]C)=[CH:19][CH:20]=2)[NH:15][CH2:14]1)[CH3:11]>>[CH3:11][N:10]([CH2:12][CH:13]1[CH2:22][C:21]2[C:16](=[CH:17][C:18]([OH:23])=[CH:19][CH:20]=2)[NH:15][CH2:14]1)[CH3:9]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 229986093-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydro-7-methoxyquinoline dihydrochloride

Product 1

HCID 219397443-(Dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinolYield 115.1%

Procedure

A solution of 3-(N,N-dimethylamino)methyl-1,2,3,4-tetrahydro-7-methoxyquinoline dihydrochloride (1.0 g) 48% hydrobromic acid (10 ml) was heated under reflux for 4 hr. The reaction mixture was poured into 10% aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried and concentrated. The resulting crude crystals were recrystallized from ethyl acetate-hexane to obtain the titled compound (0.81 g). The melting point of its dihydrochloride was 151-152° C. (recrystallizing solvent; methanol-diisopropyl ether).

Workup

  1. temperatureunder reflux for 4 hr
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe resulting crude crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0ed55f1a79e4239bf1a211b18e8ee78
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

Loading…